Fluorous triphase and other multiphase systems

Abstract

A method of reacting a first compound to produce a second compound includes the step of contacting a first non-fluorous phase including the first compound with a first fluorous phase at a first phase interface. The first compound distributes between the first fluorous phase and the first non-fluorous phase. The method further includes the steps of contacting the first fluorous phase with a second non-fluorous phase at a second phase interface and including at least a third compound in the second non-fluorous phase that reacts with the first compound to produce the second compound. The second compound has a distribution coefficient less than the first compound. This method can, for example be used to separate the second compound from unreacted first compound wherein, for example, the first compound is of a fluorous nature and distributes more readily into (or transports more quickly through) the fluorous phase than does the second compound. In general, the fluorous phase serves as a barrier to prevent the two non-fluorous phases from mixing, but molecules that can migrate through the fluorous phase can pass from one side to the other.

What is claimed is:  
     
       1. A method of reacting a first compound to produce a second compound comprising the steps of: 
       contacting a first non-fluorous phase including the first compound with a first fluorous phase at a first phase interface, the first compound distributing between the first fluorous phase and the first non-fluorous phase;  
       contacting the first fluorous phase with a second non-fluorous phase at a second phase interface; and  
       including at least a third compound in the second non-fluorous phase that reacts with the first compound to produce the second compound, the second compound having a distribution coefficient less than the first compound.  
     
     
       2. The method of  claim 1  one wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an aqueous phase. 
     
     
       3. The method of  claim 1  wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an organic phase. 
     
     
       4. The method of  claim 1  wherein the first non-fluorous phase is a first organic phase and the second non-fluorous phase is a second organic phase. 
     
     
       5. The method of  claim 4  wherein the first organic phase also includes at least one compound other than the first compound, the other compound having a distribution coefficient less than the first compound. 
     
     
       6. The method of  claim 5  wherein the other compound has a distribution coefficient substantially less than the first compound. 
     
     
       7. The method of  claim 6  wherein the first compound has a distribution coefficient in the first organic phase between approximately 0.01 and approximately 10. 
     
     
       8. The method of  claim 4  wherein the first compound includes a fluorous group and reacts with the third compound to produce the second compound that is less fluorous in nature than the first compound. 
     
     
       9. The method of  claim 8  wherein a fluorous compound resulting from the reaction of the first compound and the third compound distributes preferentially from the second organic phase into the fluorous phase. 
     
     
       10. The method of  claim 9  wherein the fluorous compound has a distribution coefficient substantially greater than 1. 
     
     
       11. The method of  claim 8  further comprising the step of tagging the fluorous group onto a precursor compound to synthesize the first compound. 
     
     
       12. The method of  claim 4  further comprising the step of contacting the second organic phase with a second fluorous phase at a third phase interface. 
     
     
       13. The method of  claim 12  further comprising the step of contacting the second fluorous phase with a third organic phase at a fourth phase interface. 
     
     
       14. The method of  claim 1  further comprising the step of perturbing at least one of the first phase interface and the second phase interface. 
     
     
       15. The method of  claim 4  further comprising the step of perturbing at least one of the first phase interface and the second phase interface. 
     
     
       16. A method of reacting a first compound to produce a second compound comprising the steps of: 
       contacting a first non-fluorous phase including a first compound with a first fluorous phase at a first phase interface, the fluorous phase including at least one fluorous reagent that interacts with the first compound to form a fluorous intermediate;  
       contacting the first fluorous phase with a second non-fluorous phase at a second phase interface; and  
       including at least a third compound in the second non-fluorous phase that reacts with the fluorous intermediate or the first compound to produce a product compound that distributes preferentially in the second non-fluorous phase.  
     
     
       17. The method of  claim 16  one wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an aqueous phase. 
     
     
       18. The method of  claim 16  wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an organic phase. 
     
     
       19. The method of  claim 16  wherein the first non-fluorous phase is a first organic phase and the second non-fluorous phase is a second organic phase. 
     
     
       20. The method of  claim 19  wherein the fluorous reagent is a catalyst. 
     
     
       21. The method of  claim 19  wherein the first organic phase also includes at least one compound other than the first compound, the other compound distributing preferentially in the first organic phase. 
     
     
       22. A method of  claim 21  wherein the second compound is substantially non-interactive with the fluorous reagent. 
     
     
       23. The method of  claim 19  further comprising the step of contacting the second organic phase with a second fluorous phase at a third phase interface. 
     
     
       24. The method of  claim 23  further comprising the step of contacting the second fluorous phase with a third organic phase at a fourth phase interface. 
     
     
       25. The method of  claim 16  further comprising the step of perturbing at least one of the first phase interface and the second phase interface. 
     
     
       26. The method of  claim 19  further comprising the step of perturbing at least one of the first phase interface and the second phase interface. 
     
     
       27. The method of  claim 16  wherein the fluorous reagent is a transport agent. 
     
     
       28. A method of separating a mixture of at least a first compound and a second compound comprising the steps of: 
       contacting a first non-fluorous phase including the first compound and the second compound with a first fluorous phase at a first phase interface, the fluorous phase including at least one fluorous reagent that selectively interacts with the first compound to form a fluorous intermediate;  
       contacting the first fluorous phase with a second non-fluorous phase at a second phase interface.  
     
     
       29. The method of  claim 28  one wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an aqueous phase. 
     
     
       30. The method of  claim 28  wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an organic phase. 
     
     
       31. The method of  claim 28  wherein the first non-fluorous phase is a first organic phase and the second non-fluorous phase is a second organic phase. 
     
     
       32. The method of  claim 31  wherein the fluorous reagent is a fluorous transport agent. 
     
     
       33. The method of  claim 31  wherein the fluorous transport agent transports the fluorous intermediate through the fluorous phase and releases the first compound into the second organic phase. 
     
     
       34. The method of  claim 31  wherein the first organic phase also includes at least one compound other than the first compound, the other compound distributing preferentially in the first organic phase. 
     
     
       35. A method of  claim 24  wherein the second compound is substantially non-interreactive with the fluorous reagent. 
     
     
       36. The method of  claim 31  further comprising the step of contacting the second organic phase with a second fluorous phase at a third phase interface. 
     
     
       37. The method of  claim 36  further comprising the step of contacting the second fluorous phase with a third organic phase at a fourth phase interface. 
     
     
       38. The method of  claim 28  further comprising the step of perturbing at least one of the first phase interface and the second phase interface. 
     
     
       39. The method of  claim 31  further comprising the step of perturbing at least one of the first phase interface and the second phase interface. 
     
     
       40. The method of  claim 32  further comprising the step of drawing off a portion of second organic phase containing the first compound and adding organic solvent that does not contain the first compound. 
     
     
       41. The method of  claim 31  further comprising the step of including a third compound in the second organic phase that reacts with the fluorous intermediate or the first compound to produce a fourth compound that distributes preferentially in the second organic phase. 
     
     
       42. A method of separating a mixture of at least a first compound and a second compound comprising the steps of: 
       contacting a mixture of the of the first compound and the second compound in a first non-fluorous phase with a first fluorous phase at a first phase interface, the first compound distributing between the first fluorous phase and the first non-fluorous phase, the second compound having a distribution coefficient less than the first compound; and  
       contacting the fluorous phase with a second non-fluorous phase at a second phase interface.  
     
     
       43. The method of  claim 42  one wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an aqueous phase. 
     
     
       44. The method of  claim 42  wherein at least one of the first non-fluorous phase and the second non-fluorous phase is an organic phase. 
     
     
       45. The method of  claim 42  wherein the first non-fluorous phase is a first organic phase and the second non-fluorous phase is a second organic phase. 
     
     
       46. The method of  claim 45  wherein the first compound is a fluorous compound. 
     
     
       47. The method of  claim 46  further including the step of selectively reacting a precursor compound with a fluorous tagging compound to produce the first compound. 
     
     
       48. The method of  claim 45  further comprising the step of including at least third compound in the second organic phase that reacts with the fluorous tagged compound to produce a fourth compound of reduced fluorous nature compared to the fluorous tagged compound, the fourth compound distributing preferentially in the second organic phase. 
     
     
       49. The method of  claim 48  wherein the fourth compound is chemically the same as the first compound. 
     
     
       50. The method of  claim 45  further comprising the step of contacting the second organic phase with a second fluorous phase at a third phase interface. 
     
     
       51. The method of  claim 50  further comprising the step of contacting the second fluorous phase with a third organic phase at a fourth phase interface. 
     
     
       52. The method of  claim 45  further comprising the step of drawing off a portion of second organic phase containing the first compound and adding organic solvent that does not contain the first compound.